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CAS No. : | 2978-10-1 | MDL No. : | MFCD28386087 |
Formula : | C14H22N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HTJDVAQGUYGUON-UHFFFAOYSA-N |
M.W : | 234.34 | Pubchem ID : | 11128254 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 72.63 |
TPSA : | 33.62 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.51 cm/s |
Log Po/w (iLOGP) : | 3.35 |
Log Po/w (XLOGP3) : | 3.12 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.92 |
Log Po/w (SILICOS-IT) : | 3.11 |
Consensus Log Po/w : | 3.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.12 |
Solubility : | 0.176 mg/ml ; 0.000752 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.49 |
Solubility : | 0.075 mg/ml ; 0.00032 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.34 |
Solubility : | 0.0107 mg/ml ; 0.0000457 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.08 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) chloride at 0 - 20℃; | |
With copper dichloride | ||
With copper(l) chloride for 72h; Ambient temperature; |
With copper(l) chloride at 20℃; | ||
Stage #1: diisopropyl-carbodiimide With tris(bis(trimethylsilyl)amido)lanthanum(III) at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzyl alcohol at 60℃; for 24h; Inert atmosphere; | 1 Example 1 10 mol% La[N(SiMe3)2]3 catalyzed diisopropylcarbodiimide and benzyl alcohol at 60°CIntermolecular addition reaction without oxygen,Under argon protection,0.3100 g (10.00 x 10-2 mol) of La[N(SiMe3)2]3 was added to the reaction flask.Then 0.81 mL (5.25×10 -3 mol) of diisopropylcarbodiimide was added and stirred at room temperature for 15 min under argon atmosphere.Continue to add another 0.52 mL (5.00 x 10-3 moles) of benzyl alcohol,The reaction was stirred in a constant temperature bath at 60°C.Remove protective gas after 24 hours,Quenching the reaction in the air,The NMR analysis of the target product isourea,Its nuclear magnetic yield is 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | for 18h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran for 18h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid 1.) THF, RT, 18 h, 2.) CH2Cl2, RT, 18 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 6% 2: 44% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 2h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 2h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In 1,4-dioxane 1) 50 deg C, 16 h, 2) 120 - 130 deg C, 0.06 mm; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In dichloromethane for 72h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Benzylalkohol, N,N'-Di-iso-propylcarbodiimid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 2: F(-) 3: dehydratation 4: reduction 5: ceric ammonium nitrate 6: 94 percent / oxalic acid / ethanol / 24 h / 22 °C 7: 50 percent / catecholborane / tetrahydrofuran; CHCl3 / 24 h / 0 °C 8: 4 M aq. HCl / dioxane / 44 h / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 2: F(-) 3: dehydratation 4: reduction 5: ceric ammonium nitrate 6: 94 percent / oxalic acid / ethanol / 24 h / 22 °C 7: 50 percent / catecholborane / tetrahydrofuran; CHCl3 / 24 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 2: F(-) 3: dehydratation 4: reduction 5: ceric ammonium nitrate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 2: F(-) 3: dehydratation 4: reduction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: F(-) 3: dehydratation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: F(-) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 2: F(-) 3: dehydratation 4: reduction 5: ceric ammonium nitrate 6: 94 percent / oxalic acid / ethanol / 24 h / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 44 percent 2: 68 percent / dicyclohexylcarbodiimide / CuCl / tetrahydrofuran / 3 h / 50 °C | ||
Multi-step reaction with 2 steps 1: 44 percent 2: 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 44 percent 2: 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 44 percent 2: diisopropylcarbodiimide / acetonitrile / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 44 percent 2: 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 44 percent 2: diisopropylcarbodiimide / acetonitrile / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexane; ethyl acetate | Benzyl 4-hydroxybenzoate (Compound Q) To a solution of 650 mg (4.7 mmol) of 4-hydroxybenzoic acid in 20 mL of tetrahydrofuran was added 1.1 g (4.7 mmol) of 2-benzyl-1,3-diisopropyl isourea. The reaction mixture was allowed to stir at ambient temperature overnight, filtered (rinsing with tetrahydrofuran) and then concentrated in vacuo. Purification by flash chromatography (silica, 25% ethyl acetate in hexane) gave the title compound as a white solid. PMR (CDCl3): δ 5.22 (1H, s), 5.35 (2H, s), 6.87 (2H, d, J=8.8 Hz), 7.34-7.50 (5H, m), 8.01 (2H, d, J=8.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With benzene In N,N-dimethyl-formamide at 80℃; for 8h; | |
75% | In N,N-dimethyl-formamide; benzene at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; for 37h; | Example 4 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-4-guanidinopentanoic acid In a dry round bottomed flask, equipped with a magnetic stirrer, 17.42 g (100 mmol) of <strong>[7200-25-1]Arg</strong>inine is added to 23.43 g (100 mmol) of the oil, N,N'-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour, the volume of the reaction is increased by the addition of 300 mL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 36 hours. The resultant mixture is then filtered in order to remove the by-product, diisopropylurea, and the THF is then evaporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, benzyl 2-amino-5-guanidinopentanoate, in pure enough form for subsequent steps. A dry, 2-necked round bottomed flask, equipped with a magnetic stirrer and a dropping funnel containing a solution of 10.83 g (52.5 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) dissolved in 60 mL of DCM, is charged with 7.80 g (50 mmol) of orotic acid, 14.54 g (55 mmol) of benzyl 2-amino-5-guanidinopentanoate, and 100 mL of DCM (all of which is under an argon atmosphere). The resultant mixture is stirred in an ice-water bath to cool the solution to a temperature of about 0 C. Following cooling, the solution of DCC from the dropping funnel is added and the reaction is allowed to warm to room temperature and then to stir overnight. The mixture is then filtered through a Celite plug and the filtrate is purified by flash chromatography (ethyl acetate/hexanes; 1/3) to yield the benzyl protected orotate amino acid amide, benzyl 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-5-guanidinopentanoate. Lastly, in a single-necked round bottomed flask, 12.06 g (30 mmol) of the benzyl protected orotate amino acid amide is dissolved in 80 mL of a mixture of methanol and tert-butanol (1:1; molar). The catalyst Palladium hydroxide on carbon [Pd(OH)2/C] is added to the mixture, the flask is then sealed with a septum, and purged with hydrogen gas. The reaction is then stirred for 3 hours under a hydrogen atmosphere, and then filtered through Celite. The filtrate is then concentrated in vacuo and then purified by flash chromatography (ethyl acetate/hexanes; 1/5) to yield 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-4-guanidinopentanoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 49h; | 5 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamide)-3-phenylpropanoic acid Example 5 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamide)-3-phenylpropanoic acid In a dry round bottomed flask, equipped with a magnetic stirrer, 13.22 g (80 mmol) of Phenylalanine is added to 18.75 g (80 mmol) of the oil, N,N'-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour the volume of the reaction is increased by the addition of 350 mL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 48 hours. The resultant mixture is then filtered in order to remove the by-product, diisopropylurea, and the THF is then evaporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, benzyl 2-amino-3-phenylpropanoate, in pure enough form for subsequent steps. A dry, 2-necked round bottomed flask, equipped with a magnetic stirrer and a dropping funnel containing a solution of 10.83 g (52.5 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) dissolved in 60 mL of DCM, is charged with 7.80 g (50 mmol) of orotic acid, 15.32 g (60 mmol) of benzyl 2-amino-3-phenylpropanoate, and 100 mL of DCM (all of which is under an argon atmosphere). The resultant mixture is stirred in an ice-water bath to cool the solution to a temperature of about 0° C. Following cooling the solution of DCC from the dropping funnel is added and the reaction is allowed to warm to room temperature and then to stir overnight. The mixture is then filtered through a Celite plug and the filtrate is purified by flash chromatography (ethyl acetate/hexanes; 1/3) to yield the benzyl protected orotate amino acid amide, benzyl 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-3-phenylpropanoate. Lastly, in a single-necked round bottomed flask, 15.74 g (40 mmol) of the benzyl protected orotate amino acid amide is dissolved in 80 mL of a mixture of methanol and tert-butanol (1:1; molar). The catalyst Palladium hydroxide on carbon [Pd(OH)2/C] is added to the mixture, the flask is then sealed with a septum, and purged with hydrogen gas. The reaction is then stirred for 5 hours under a hydrogen atmosphere, and then filtered through Celite. The filtrate is then concentrated in vacuo and then purified by flash chromatography (ethyl acetate/hexanes; 1/5) to yield 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamide)-3-phenylpropanoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 49h; | 5 Example 5; 2-(2,6-dioxo-l ,2,3,6-tetrahydropyrimidine-4-carboxamide)-3-phenylpropanoic acid (Phenylalanine Orotate); In a dry round bottomed flask, equipped with a magnetic stirrer, 13.22g (80mmol) of Phenylalanine is added to 18 75g (80mmol) of the oil, A^TV-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour the volume of the reaction is increased by the addition of 35OmL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 48 hours. The resultant mixture is then filtered in order to remove the by-product, dϖsopropylurea, and the THF is then ev aporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, benzyl 2-amino-3-phenylpropanoate, in pure enough form for subsequent steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 37h; | 4 Example 4; 2-(2,6-dioxo-l,2,3,6-tetrahydropyrimidine-4-carboxamido)-4-guanidinopentanoic acid (Arginine Orotate); In a dry round bottomed flask, equipped with a magnetic stirrer, 17.42g (lOOmmol) of Arginine is added to 23.43g (lOOmmol) of the oil, yV,iV'-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour, the volume of the reaction is increased by the addition of 30OmL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 36 hours. The resultant mixture is then filtered in order to remove the by-product, diisopropylurea, and the THF is then evaporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, ben/yl 2-amino-5-guanidinopentanoate, in pure enough form for subsequent steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetonitrile at 120℃; for 0.0833333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In N,N-dimethyl-formamide; benzene at 80℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In 1,4-dioxane at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In 1,4-dioxane at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.691 g | Stage #1: L-Asp(t-Bu); 2-nitrobenzyl chloride With triethylamine In dichloromethane at -78 - 20℃; Stage #2: O-benzyl-N,N'-diisopropylisourea In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In tetrahydrofuran at 60℃; | 1 Compound 14 : Fmoc-Cys(MMt)-OH 13 (3g, 4.9 mmol.) and 1 ,3-diisopropyl-2-benzylisourea (2.4 g, 12.2 mmol.) were dissolved in dry THF (120 ml_) and heated at 60 °C overnight. Then, the reaction was extracted with EtOAc (100 ml_) and 10% HCI aqueous solution (50 mL). The organic phase was dried over magnesium sulphate and evaporated to dryness under reduced pressure. The crude reaction mixture was purified by silica gel column chromatography using Hex: EtOAc (8:2) as eluent to afford Fmoc-Cys(MMt)-OBn 14 as a yellow solid (2.6 g, 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 60 °C 2: piperidine / N,N-dimethyl-formamide / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / 60 °C 2: piperidine / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: dichloromethane / 100 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrahydrofuran / 60 °C 2: piperidine / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: dichloromethane / 100 °C / Sealed tube 4: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrahydrofuran / 60 °C 2: piperidine / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: dichloromethane / 100 °C / Sealed tube 4: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5: N,N-dimethyl-formamide; aq. phosphate buffer / 3 h / 20 °C / pH 7.4 |
Tags: 2978-10-1 synthesis path| 2978-10-1 SDS| 2978-10-1 COA| 2978-10-1 purity| 2978-10-1 application| 2978-10-1 NMR| 2978-10-1 COA| 2978-10-1 structure
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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